Thinking about Dennis being afraid of Jack getting turned off from seeing his bottom growth, only for the older man to pull out his own, significantly bigger t-dick.
He steps closer to inspect the boys cock before aligning their bodies so their crotches rub against each other.
The sight of their cocks squished together makes Dennis let out a loud keen.
It's obscene how Jack's dwarfs his, and all his insecure thoughts are replace by a need to suck the man off. He tries to say as such, but in his excitement only a string of gurgles and groans comes out.
Jack scoffs at how needy the boy is " Well, Whitaker, you have a lot of growing to do. It's a pretty little thing-" he puncuates it with a sharp thrust before continuing, "just like its owner. But maybe once you're older you'll have a nice manly cock just like me-"
He grinds down harder, emphasizing just how miniscule the boy's dick looks in comparision to his own.
Dennis is mesmerized by it, letting out a stream of incomprehensible noises through his open mouth.
Jack grins, amused by how quickly the resident fell apart. "Shit, puppy. If you think my cock is big, you should see Robby's"
The way Dennis' dick twitches lets him know just how much the boy likes that idea.
"You did what?!"
"You better be grateful Brother, I'm bringing your favourite boy straight to your bed. Or couch, seems like he might be too desperate to wait that long."
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The door clicked shut with a soft thud, sealing off the worst of the noise. Still, the bass from the downstairs speakers thrummed through the floorboards, vibrating right up into the soles of Robby’s beat up converse.
Jack had shoved past the crowd, grabbed Robby by the elbow, and essentially dragged him up the stairs without a single word of explanation. Robby had only followed because Jack looked genuinely pissed, but regret was setting in fast. They were standing in one of the upstairs bedrooms, and a random frat house bedroom was the absolute last place Robby wanted to be under any circumstances. The room smelled faintly of stale beer and cheap air fresher, and the floor was so littered with trash it looked like a raccoon had set up residence.
“What’s going on with you, man?”
Robby forced his eyes away from a suspicious pile of dirty laundry in the corner and looked at Jack. His roommate was flushed, sweaty, a few stray auburn curls sticking to his forehead.
“What? You dragged me in here.” Robby tugged at his t-shirt. The cotton had glued itself to his back and ribs from the heat downstairs. Honestly, he was a little grateful for the quiet break, even if the atmosphere in the room felt suddenly suffused with tension.
“Because something is going on with you.” Jack sounded genuinely upset, his forehead creased. Robby had never been more confused in his life. “What happened downstairs with Maddy?”
Oh.
“Nothing happened.”
“Exactly. You’ve been making puppy eyes at the girl for weeks, she finally gives you a shot, and you completely bolt. What was that about?”
Robby shrugged, his shoulders practically hitching up to his ears. He really, really didn't want to talk about this—especially not with Jack. Even though they’d gotten along great since being assigned as dorm mates at the start of the semester, Robby still kept his guard up. He had to be careful about who he let in.
“I wasn’t feeling it.”
“Bullshit. You two were making out against the wall and you were literally grabbing her ass.”
“Doesn’t mean I wanted to fuck her.” The pitch of Robby’s voice spiked an octave, and he instantly hated how defensive it made him sound.
“Are you scared or something?” Jack let out a short, incredulous laugh, but the sound died in his throat the second he caught the look on Robby’s face. The smile vanished. “Wait...you were scared? What for, man? It’s not like you’re a virgin.”
“For sure,” Robby muttered dismissively. He reached up to scratch at his neck, pulling at his shirt again. The room suddenly felt five degrees hotter, his clothes way too tight.
“Are you...wait, are you a virgin?” Jack searched his face, sounding bewildered, like Robby was playing some kind of elaborate joke on him. “What about Emma? You fucked her, didn’t you?”
Robby just shrugged again. He’d gotten Emma off. She’d been great, too—sweet, funny, and incredibly understanding when Robby had awkwardly asked if they could leave his clothes on.
“She spoke wonders of you, man.”
“Can we drop this topic, Jack? It’s really none of your business.”
Robby made a move to step around him, reaching for the doorknob—only to realize Jack had quietly locked it behind them. Before he could turn the handle, Jack planted a broad palm flat against Robby’s stomach, effectively slotting his body into the space between Robby and the exit.
“It is my business, you know?” Jack said. “I can hear you jerk off at night, man.”
“What?” A wave of heat flooded Robby’s face so fast he was convinced he was about to physically combust right there on the carpet. “What the fuck, Jack? Why didn’t you say anything sooner?”
“I thought you’d get it out of your system. Thought you were just on a dry streak.” Jack didn't pull away. He held Robby’s gaze for a few agonizingly long seconds, his palm heavy and warm through Robby’s top. “What are you actually scared of? Performance issues? Because you can certainly go a while, from what I’ve heard.”
Robby looked away, his pulse hammering in his ears as he swallowed hard past a tight lump in his throat. The worst part was that even now, paralyzed by mortification, he was still turned on. The heat from making out with Maddy downstairs hadn't fully left his system, it was still simmering low in his gut. Having Jack standing this close, breathing the same hot air, was only fanning the embers.
“It’s none of that,” Robby finally muttered under his breath, staring stubbornly at Jack’s collarbone.
“Then what is it?”
“Can you promise you won’t be weird about it?”
Jack nodded, his messy curls bouncing slightly. He bit his bottom lip with slightly uneven front teeth, a tiny habit that distracted Robby just long enough to gather his courage. He had to get this over with. Jack wasn't going to drop it until he got a real answer anyway.
Even so, the actual explanation caught violently in Robby’s throat. He had never been good at vocalizing it—never knew how to put it into words without feeling exposed. It was the exact reason he’d panicked and bolted the second Maddy invited him up to a room.
With a trembling hand, Robby reached down and wrapped his fingers around Jack’s wrist. Slowly, he guided Jack’s hand lower.
He braced himself for Jack to resist—to shove him back, laugh, or punch him. Honestly, any of those reactions would have made sense given that Robby was physically dragging his hand down toward his crotch. But Jack didn't fight it. He just stared at Robby with wide, stunned eyes, allowing his hand to be guided until his palm rested flat over the front of Robby’s jeans. The subtle flex of Jack’s fingers sent a sharp, electrifying shiver straight down Robby’s spine. Nobody had ever touched him like that.
Jack’s fingers tightened slightly, pressing down, his lips parting as he registered the complete lack of a bulge beneath the denim.
This is it, Robby thought, his breath coming in shallow hitches. This was where the violence came. This was where Jack pulled away in disgust, and Robby got reminded of his place. He kept his hand loosely looped around Jack’s wrist, waiting for the blow. They were standing so close their chests were practically brushing, sharing the exact same air. But Jack didn't pull away. Instead, his fingers flexed again, shifting over the denim, making Robby shudder with a sudden, dizzying spike of arousal. He felt sick to his stomach, terrified he was going to throw up if Jack didn't break the silence.
“This...this has been the issue all along?” Jack finally asked. He slowly pulled his hand back, but his expression wasn't angry or disgusted. In fact, his face was completely unreadable.
“It’s a pretty damn big issue,” Robby rasped, pulling his own hand back to wrap defensively around his waist.
“I don’t know, man.” Jack scratched the back of his neck, his eyes roving over Robby’s face. “A lot of girls are into pussies. And...you like guys too, right? I’m sure you could easily find a guy to fuck you if you’re into that.”
Robby opened his mouth, closed it, and stared. Jack hadn't moved an inch, his chest was still hovering just centimeters away.
“If you find a guy who can fuck me and actually keep his mouth shut about it, send him my way,” Robby hissed, a sudden rush of defensive annoyance cutting through his panic. “You think anyone at this party is gonna keep it to themselves if they find out Robby doesn’t have a dick?”
“I know someone.”
“Yeah? Who?” Robby rolled his eyes, dragging a hand over his face. His skin was still burning, he’d just found out his roommate listened to him touch himself at night, he’d forced Jack to feel him up, and the entire night was spiraling out of his control way too fast to catch. He shouldn’t had done that third round of shots.
Jack tilted his head, his dark eyes locking onto Robby’s with an intensity that made Robby’s heart drop into his stomach.
“You know him very well.”
Jack’s words hung in the thick air between them. Robby’s pulse stuttered.
“You…” The single syllable came out cracked. He tried again. “You’re serious.”
Jack just kept looking at Robby like he was seeing him for the first time and deciding, very carefully, that he liked what he saw.
“I’ve known for a while,” Jack said quietly. “Not the details. Just…that something was off. The way you never changed in front of me. The way you always kept the lights low.” His voice dropped even lower. “And yeah. I’ve listened. More than I should have.”
Robby’s throat worked. The confession should have made him want to crawl under the nearest pile of dirty laundry and never come out. Instead it sent another slow, unwanted pulse of heat straight between his legs. He was still horny from Maddy, still buzzing from the shots, and Jack’s hand had been on him—really on him—only moments ago. The memory of those fingers pressing down where there was nothing to press against made his knees feel unreliable.
“Why didn’t you say anything?” He asked.
“Because it wasn’t my business until you made it mine.” Jack’s gaze flicked down, just once, to the front of Robby’s jeans, then back up. “So now I’m asking. Do you want me to leave, or do you want me to stay?”
Robby should have said leave. He should have unlocked the door and gone back to the party and pretended this never happened. Instead he heard himself answer, voice barely above a whisper.
“Stay.”
Jack exhaled like he’d been holding his breath. He stepped closer—close enough that Robby had to tip his chin down to keep eye contact. The height difference had never felt this charged before. Jack’s palm came up again and settled against the side of Robby’s neck. Thumb brushing the hinge of his jaw.
“Can I kiss you?”
Robby’s answer was to fist a handful of Jack’s damp t-shirt and pull.
The first press of mouths was careful, almost hesitant. Jack tasted like cheap beer and Robby made a small, involuntary sound when Jack’s tongue slid against his and crowded him backward until his shoulders hit the door. The handle dug into his spine. He didn’t care.
Jack kissed like he’d been thinking about it for a long time—wet, dirty, one hand still cupping Robby’s face while the other slid down to rest at his waist.
“Tell me if anything’s off-limits,” Jack murmured against his mouth. “I mean it.”
Robby’s laugh came out shaky. “Shut the fuck up.”
Something in Jack snapped at the order. He kissed harder, messier, teeth catching Robby’s lower lip as he shoved him away from the door and toward the bed like he couldn’t stand another second of standing still.
Robby stumbled backward, still fisting Jack’s shirt, until the backs of his knees hit the mattress. He went down hard, bouncing once on the creaky twin bed. The sheets smelled like laundry detergent and someone else’s body spray. Jack followed immediately, climbing over him, hands already at the waistband of his jeans.
“Off,” Jack muttered against his mouth, impatient, tugging. “Fucking—off.”
Robby’s head was spinning. The shots, the heat, the way Jack’s weight pinned him down—everything felt too fast. His brain kept looping the same panicked half-thoughts: This is happening. This is actually happening. He’s going to see. He’s going to—
But his body wasn’t listening. When Jack yanked at his shoes, Robby lifted his feet without thinking. Converse hit the floor with two dull thuds. Then Jack’s fingers were at his button, popping it open, dragging the zipper down in one rough pull. He hooked his hands under the denim and the waistband of Robby’s briefs and hauled everything down in one go—jeans, underwear, all of it—shoving the fabric past his thighs and off his ankles like it personally offended him.
Cool air hit Robby’s bare skin. He made a small, choked sound and tried to close his legs on instinct.
Jack didn’t let him.
He pushed Robby’s knees apart with both hands, settled between them on his stomach, and looked. Just looked, for one long second that felt like forever. Robby’s face burned. He could feel how wet he already was, how obvious it had to be.
Jack just leaned in and put his mouth on him.
Robby’s whole body jerked. A sharp, broken noise tore out of his throat as Jack’s tongue dragged up through his folds, broad and wet and completely unhesitating. No teasing or a slow build. Just hungry, messy pressure right against his clit, then lower, licking into him like he’d been starving for it.
“Jack—fuck—” Robby’s hands flew to Jack’s hair on pure reflex, fingers tightening hard enough to pull. His hips tried to twist away and push closer at the same time.
Jack only groaned against him and sucked harder, sealing his mouth over Robby’s clit and working it with his tongue in short, filthy strokes. One of his hands stayed locked on Robby’s thigh, keeping him spread open. The other slid up under Robby’s shirt, palm flat against his stomach, grounding him while he ate him out like he had something to prove.
Robby’s head tipped back against the thin pillow. His mouth fell open. Every wet sound Jack made was loud in the quiet room—louder than the muffled music still thumping up through the floor. He could feel how soaked he was already, how easily Jack’s tongue slid through him, how shamelessly his body was responding even while his brain kept throwing up weak little protests that never quite stuck.
Jack flattened his tongue and licked a long, deliberate stripe from entrance to clit, then sealed his lips around the swollen bud and sucked again, harder. Robby’s thighs trembled. A high, helpless sound slipped out of him before he could bite it back.
His hips kept stuttering up against Jack’s mouth, chasing every wet drag of tongue, but the need building under his skin was too sharp, too restless. He couldn’t just lie there and take it anymore. With a rough, desperate sound he shoved at Jack’s shoulders, fingers still tangled in the auburn curls, and hauled him up the length of his body.
Jack came willingly, mouth shiny, breathing hard. The second he was close enough Robby’s hands were already at his jeans, clumsily popping the button and dragging the zipper down with a metallic snarl. He shoved the denim and boxers down just far enough to free Jack’s cock. It was thick, flushed dark, already leaking at the tip. Robby wrapped his fingers around it without hesitation and stroked, tight and a little too fast, spreading the precome over the head with his thumb.
Jack cursed under his breath, forehead dropping against Robby’s. His hips gave an involuntary twitch into the grip.
“Fuck—Robby—”
Robby kept working him, wrist twisting on the upstroke, watching the way Jack’s jaw went tight. The heat of him in his hand made Robby clench around nothing. He was soaked, thighs sticky, and every nerve was screaming for more than just a tongue.
Jack’s hand came up to still Robby’s wrist after a few more strokes. His voice was rough.
“Hey. We don’t have to— I mean, if you want to go slow with the rest of it. First time and everything. We can just—”
“I’ve used toys,” Robby cut in, the words tumbling out before he could second-guess them. His face burned, but he didn’t look away. “I’m not— I know what it feels like. I just…I want you. Now.”
Jack stared at him for a second, something hot and almost disbelieving flickering across his face. Then he was scrambling for his back pocket, yanking out a condom like it was the most important thing in the room. He tore it open with his teeth, rolled it on with quick, shaky fingers, and settled back between Robby’s spread thighs.
The blunt head of Jack’s cock nudged against him. Robby’s breath caught. He was wet enough that the first slow push met almost no resistance—just a stretch, a pressure that made his stomach flutter. Jack sank in maybe an inch and stopped, eyes locked on Robby’s face.
“You good?”
Robby nodded, but his body had other ideas. The moment the thicker part of the head started to breach him he locked up, thighs tightening, breath going shallow. It wasn’t pain exactly. Just too much, too new, the reality of being filled by someone else’s cock instead of silicone hitting him all at once.
Jack felt it immediately and went still, one hand stroking up and down Robby’s side under the rucked-up t-shirt, the other braced by his head.
“Breathe,” he murmured. “I’ve got you. We can stop.”
“Don’t stop.” Robby’s voice came out thin. He forced his legs to open wider, forced the tension out of his hips even though every instinct wanted to clamp down. “Just…slow. Please.”
Jack nodded once and pressed forward again, careful, giving Robby time to adjust around every new inch. The stretch burned in a way the toys never quite had—hotter, thicker, alive. Robby’s fingers dug into Jack’s shoulders hard enough to make the fabric strain. He clenched and fluttered around the intrusion, still trying to decide whether to push him out or suck him deeper. The wetness made the slide easy once the initial lock-up eased, but the sensation of being opened up like this—of Jack’s weight above him, the careful roll of his hips—made Robby’s eyes sting.
When Jack finally bottomed out he stayed there, breathing hard against Robby’s neck.
“Christ. You’re—fuck, you’re tight.”
Robby couldn’t form words. He just nodded against Jack’s shoulder, hips giving a tiny, involuntary roll that made both of them hiss. The fullness was overwhelming. His first time with a real cock and it already felt like too much and not enough at the same time. He was still shaky, still half-convinced this was going to end badly any second, but the desperate, greedy part of him that had been aching all night just wanted Jack to move.
Jack waited until Robby’s breathing evened out a little, until the white-knuckled grip on his shoulders loosened. Only then did he draw back a few inches and push in again—slow, deep, testing.
Robby’s mouth fell open on a broken sound.
Jack kept the pace deliberate, deep rolls of his hips that dragged every inch of him against Robby’s walls. He was trying. God, he was trying. His jaw was tight with the effort of holding back, forehead pressed to Robby’s temple as he worked himself in and out with careful control. But it felt too good. The wet heat of Robby’s pussy, the way it fluttered and clenched around him every time he bottomed out, the soft broken sounds spilling out of Robby’s mouth—none of it was making restraint easy.
Robby’s hands slid up Jack’s back, then higher, fingers curling into the damp curls at the nape of his neck. He tugged, pulling Jack down until their mouths met again. The kiss was messy from the start, more tongue than finesse. Robby made a needy little noise into it and rolled his hips up to meet the next thrust, taking Jack deeper.
That was all it took.
Jack’s rhythm stuttered. He tried to recover, tried to keep the slow slide, but Robby’s mouth was open under his and he was gripping him so tight and perfect that the careful control simply snapped. He drove in harder. Faster. The next thrust punched a sharp gasp out of Robby, and then Jack was fucking him properly with short, powerful strokes that made the cheap bed frame creak and the headboard start knocking against the wall in a steady rhythm.
Robby’s legs locked around Jack’s waist instead, heels digging into the small of his back, pulling him in deeper with every hard snap of hips. The stretch that had felt overwhelming minutes ago now just felt necessary. The sound of it all was filthy under the wet slap of skin and the relentless thud of the headboard.
Jack groaned into the kiss, lost, one hand braced by Robby’s head while the other shoved under his ass to tilt him higher. The new angle made every thrust drag right over the spot that made Robby’s vision spark white at the edges. He broke the kiss with a choked-off moan, forehead pressed to Jack’s, breath coming in short, punched-out bursts.
“Jack—fuck, Jack—”
Jack didn’t slow down. Couldn’t. The careful, considerate version of him had been left somewhere three thrusts ago. Now he was just chasing the tight heat of Robby’s body, fucking into him hard and deep while the headboard kept announcing exactly what they were doing to anyone who might be listening in the hallway.
Robby was still shaking a little—first-time nerves mixed with pure, overwhelming sensation—but he couldn’t even think about stopping or slowing down. He just held on and took every hard, relentless thrust. It was so much better than he could’ve ever imagined.
Jack was buried so deep it felt like he was rearranging something inside him, and Robby’s body kept clenching around the thick length, trying to keep him there. The friction against his clit with every snap of hips was sharp and perfect and almost too much.
Fuck—Robby was going to come. Jack was going to make him come on his cock during his first time and—
The thought cut off when Jack shifted the angle again, shoving one of Robby’s thighs higher against his own side. The next thrust dragged deeper inside him and Robby’s whole body arched, a high, helpless noise tearing out of his throat. His pussy fluttered hard around Jack’s cock.
Jack cursed, voice wrecked. “Shit—you feel—fuck, Robby—”
He fucked harder, chasing the way Robby’s body kept tightening around him. The headboard slammed into the wall even louder now with every thrust. Robby couldn’t bring himself to care. He was too far gone—legs locked around Jack’s waist, mouth open against his shoulder, taking every stroke like he was starving for it.
Jack’s hand slid between them, fingers finding Robby’s clit and rubbing in tight, messy circles that matched the pace of his hips. The sensation ripped through Robby like a live wire. His back bowed off the mattress. The tension that had been coiling low in his gut snapped all at once.
He came hard—clamping down in pulses around Jack’s cock, thighs shaking, a broken, desperate sound muffled against Jack’s neck. His vision went blurry at the edges. The orgasm rolled through him in waves, longer and sharper than anything he’d managed alone or with toys, leaving him trembling and gasping under Jack’s weight.
Jack followed almost immediately. The way Robby’s body gripped him was too much. He buried himself with a low groan and came, hips stuttering through it, forehead pressed hard against Robby’s as he rode it out.
Robby’s brain was blank as he stared up at the water-stained ceiling and tried to remember how to breathe.
Jack stayed inside him for a long moment, weight heavy and warm, breath still coming in uneven pulls against the side of Robby’s face. Neither of them moved. The room smelled like sex and sweat and the sweet cologne that had been on Jack’s skin all night. Something that must’ve rubbed off on him from some girl.
Eventually Jack shifted, careful. He braced himself on one forearm and looked down at Robby’s face, eyes searching.
“You okay?” His voice was rough, quieter than usual.
Robby’s thighs were still trembling. He could feel the way Jack was starting to soften inside him, the slick mess between them. His fingers were still loosely curled against Jack’s back, tracing idle, uncoordinated paths over damp cotton. But he nodded. The motion a little uncoordinated. “Yeah. Just…a lot. But good.”
Jack’s mouth twitched, almost a smile, but there was something softer underneath it. He reached down between them, holding the base of the condom as he eased out. Robby sucked in a sharp breath at the sudden emptiness, at how his body clenched around nothing. A thin trickle of slick followed, sliding down the curve of his thigh onto the sheets. He felt exposed in a way that had nothing to do with just being naked.
Jack tied off the condom and dropped it somewhere off the side of the bed without looking, then immediately came back, settling on his side next to Robby instead of on top of him.
“You locked up at the start,” Jack said after a minute, voice low. “I was worried I was hurting you.”
“You weren’t.” Robby stared at the ceiling for a second longer, then turned his head to look at him. The honesty felt strange in his mouth, but the post-orgasm haze made it easier. “It was good.”
The word good felt inadequate for the way his body still hummed, for the strange, floating calm that had settled over the sharp edges of panic. He shifted carefully onto his side so they were facing each other on the narrow mattress.
Jack’s hand found the hem of Robby’s still-rucked-up t-shirt and smoothed it down over his stomach without comment, like he was trying to give him back a little privacy. The gesture was almost tender.
“Yeah?” Jack asked. His voice was still rough. One auburn curl stuck to his forehead. Robby had the sudden, absurd urge to brush it away. “Because I kind of lost it there at the end. Wasn’t exactly gentle.”
“I noticed.” Robby’s mouth twitched. He could still feel the echo of those last hard thrusts. “Didn’t want gentle by then.”
Jack exhaled a short laugh that sounded half relief. He propped himself up on one elbow, looking down at Robby with an expression that was harder to read than usual. “We should probably get dressed before someone tries the handle,” he murmured.
Robby groaned softly but nodded. Sitting up made every muscle protest. He found his underwear and jeans in a heap near the foot of the bed and dragged them on with less grace than usual. The denim felt too tight against still-sensitive skin. Jack watched him the whole time, open and unhurried, as he fixed his own clothes.
When Robby’s gaze drifted back to the bed, the wet patch on the sheets glared up at him like an accusation. He’d lost his virginity on some poor frat bro’s bed—to Jack, of all people. His roommate. The thought sat heavy and slightly absurd in his chest.
“Just a laundry load,” Jack muttered, already reaching for a pillow and tossing it over the spot with casual precision. “At least it’s not blood.”
A stupid, helpless laugh bubbled out of Robby before he could stop it. He finished tying his shoes with fingers that felt slightly clumsy, the leftover embarrassment still humming under his skin like a second pulse.
Jack paused at the door, one hand on the frame. “I’ll see you downstairs.”
“Yeah,” Robby nodded, chewing the inside of his lip. He had no intention of seeing Jack again tonight. He was going to slip out of this party, head straight back to their dorm, and pretend the last hour hadn’t happened. Even as he thought it, he was already aware of how thoroughly inconvenient it was that he’d just fucked his roommate.
Old trans bear Robby who doesn’t think he’s desirable anymore and cis Dennis who literally cannot get enough of him.
“Fuck, Daddy, y’re so good, taste so good.” Dennis babbles, face buried in Robby’s cunt. He’s near tears, all his dreams in life coming true at once.
Robby hasn’t experienced this type of pleasure in years. Dennis’s mouth forms a beautiful suction around his tdick, hot and wet and utterly addicting. He buries his hands in Dennis’s curls, keeping him right where he wants him.
“Good boy, good fucking boy. You’re such an eager puppy, huh?” Dennis moans and bucks his hips into the mattress, and if he had a tail it would be wagging nonstop. Robby just chuckles at him. “My puppy.”
Dennis doesn’t stop eating him out, he couldn’t if he tried. He loves making Robby feel good, more than he likes feeling good himself. He could stare at Robby forever and never once get tired. The amount of times he’d jerked off to pictures of his Daddy was innumerable, Dennis couldn’t picture a hotter man. A good amount of meat on his bones, a big, soft, hairy belly. Pecs that were large and soft even after surgery. A thick beard and wrinkles that showed a full life.
“You’e humping the bed like a dog, huh?” Robby said gruffly. Dennis whined.
“‘M Daddy’s puppy. Daddy’s so hot, I want, I want it.” Dennis’s head feels fuzzy and full of cotton, his only goal in life being to find out how to live off of Robby’s cunt alone.
It was a strange learning curve for the older man, since he had grown so used to being passed over by young pretty boys like Dennis. Many a time he had bought a boy a drink only to have their faces scrunch up upon learning that not only is he trans, but he never got a phalloplasty. He had expected the same from Dennis, maybe even the “I’m not into women.” talk he had heard before. It didn’t make him dysphoric anymore, thankfully, but it did send a spark of anger through him. What he did not expect was for Dennis to cum in his pants as soon as he saw Robby’s naked body.
feeling bold time to post some bullshit i already mentioned in my discord server
needy sub (cis) dennis who's inexperienced and shy and soft dom trans daddy robby who teaches dennis how to fuck him but dennis is just sooooooo sensitive he keeps cumming so fast :( and he's so sad and upset about it because he wants to make daddy cum :( he wants to be a good boy and last long enough for daddy :( but he just can't it just feels too good he can't help it :(
and robby coos and tells him it's okay while he's sniffling and crying in his arms apologizing for finishing too quick again like "don't be sad baby, you're getting better. you held on longer than last time didn't you? you'll be fucking daddy real good in no time sweetheart."
but yeah dennis is sooooooooo fucking easy
like when he eats robby out his boxers (or panties hehehe) are wrecked in like 90 seconds cuz he's so turned on he's just leaking cum the whole time he's sucking and licking at daddy's cunt <3
and he's not strictly a top so when robby pulls out the strap dennis is going ham on that thing
he'll suck it and whimper on it or ride it like he's trying to obliterate his own pelvis and robby praises him for taking it so well and he knows dennis doesn't need or want a break between orgasms so he just keeps pounding until he tires himself out and that's when dennis starts begging for more and robby has to use his firm voice to tell his baby they both need to let their bodies rest
and dennis begging to fuck daddy's pussy all the time always promising he can hold out for more than a few minutes this time and they both know damn well that's not true but robby doesn't mind cuz he loves feeling his baby boy's pretty little cock thrusting deep inside him, the warm gush when dennis inevitably lets loose early, and the sticky fluid leaking out of him that dennis will lap up like candy after he finishes crying
and the aftercare is robby's favorite part when he gets to take care of his baby boy and kiss him and tell him how good he did and they snuggle up
it's during one of these aftercare cuddle sessions that they first tell each other i love you
Give me old trans man Robby. Robby who transitioned in the 90s.
Robby who started going by Robby cause 1) it was masculine 2) it eased the name change and 3) he was already pressured to shorten Robinavitch might as well make it useful.
Robby who had shit transition healthcare (as was very common at the time) and is only alive cause he was in med school. Who, like a lot of people, ended up on unsafe forms of hormones cause they didn't know the safety at the time (like pills). Who nearly was chronically overdosed on T cause there were next to no docs who knew how to competently treat a trans patient. Robby who had to do so much endocrinology research to help himself and later the other trans people around him.
Robby who's push to being an ER doc was cause he had to help his trans community since no one wanted to treat them. Who saw how much he could help when he was on his ER rotation. Who saw how his friends were treated and decided to have all of them come to him instead no matter how busy he was.
Robby who had to work through the height of the AIDS crisis and watch as his community was failed by everyone around him. Robby who saw how the other doctors and nurses talked about and treated trans and especially trans HIV patients but had no standing to combat it at the time. Robby who ended up being requested by queer and HIV patients cause even if they didn't know he was queer they did know he was safe.
Robby who has been out so long he still idenfies as transexual. Robby with phaloplasty. Robby who got top surgery prior to chest masculinization really being an option. Robby with fucked up ribs cause chest binders didn't exist yet so your option was only unsafe binding.
Robby who is stealth at work cause he's so used to having to hide that part of himself for saftey. Robby who still has to hide that part of himself for saftey even now and hates that the world hasn't changed since the 90s.
Robby who sees Whitaker just starting his transition and makes sure he never has to deal with any of the bullshit he did. Robby also being with Trinity in lowkey (lovingly) flaming him for choosing to be named Dennis.
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TW: deadnaming, the name itself and the event isn’t described, just mentioned.
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Jack and Robby both start growing out their beards while working the same shift. Robby’s quietly proud—it’s the first time since starting t that his beard actually started to look like a “real” beard.
However, after admins make a whole deal out of being professional and looking presentable. Adamson tells them one of them has to shave—“Not running a biker gang on day shift. Patients and upstairs prefer clean-shaven doctors, gentlemen.”
and somehow Robby’s and Jack’s already fragile dynamic grows a little more tense as neither of them wants to shave.
They bet on it, the person who works on the most patient in a month won’t have to shave his beard. As time passes, their stupid bet over who has to shave their beard continues—both of them putting in longer hours sometimes to catch up with the other one.
Jack is just doing this to piss robby off and show him that he’s better than him, blissfully unaware of the fact that the beard represents something more important to robby
After a confrontation with a patient, out of nowhere Robby spirals, staggers back into the hub and finds Jack. Stoic Mr. Robinavitch seems to be lost, his face pale as he asks Jack to take over his patient for him.
Jack could do nothing but nod due to the man’s demeanor all shaken up. When Jack got over to check the patient, she seemed like a regular old patient, nothing out of the ordinary. So he had no idea why Robby passed the patient to him and looked like he was about to puke his guts out.
Later on, as the hours pass by, he tries to ask Robby what actually went down with the patient.
“What, did she flirt with you or something? What got your panties all tied up?” Jack says as he tries to lighten the mood and figure out what actually happened.
He somehow finds himself worried about Robby.
However, Robby isn't having any of it. He snaps at Jack, clearly overwhelmed, tears and frustration brimming in his eyes and his face ashy like the chalk they use on blackboards—his pale face a stark contrast to his brown beard.
Jack thinks, screw this, we aren’t really friends anyway, so why should he care, anyway? But Jack can’t still forget the look in Robby’s eyes.
Robby takes rest of the day off.
The next day, Robby shows up clean-shaven, eyes puffy, his face sunken.
Jack doesn’t fully understand why the man shaved and admitted defeat this early.
Also, why did a beard matter so much in the first place anyway?
Then one day, he overhears Robby whispering to Dana about being deadnamed in his medical records and how he feels like he doesn’t ‘look’ masculine anymore, and yeah, Jack feels like the biggest asshole.
While Jack never clocked that Robby was trans, but he was still able to understand why Robby might feel like he wasn’t ‘enough’.
To jack he was more than enough. He was Robinavitch fo g-d’s sake. A man who could do everything, an unwavering force.
Even though Jack had no idea what went down with that patient months ago, he was now somewhat sure that it must have been something related to Robby being trans, Especially since the poor guy shaved his beard the day right after that encounter.
Next shift, Jack shows up clean-shaven.
He doesn’t make a big deal out of it—just hands Robby a small bottle of beard oil and shrugs — “You should grow it back, brother. Looks better on you anyway.”
Robby’s beard grows faster this time around and jack never stops buying him that brand of expensive beard oil.
jack finding out that robby has a pretty pussy. jack being the only one robby has told that he's trans except for his grandma. so jack did what he do best, he ate out robby until the poor man is screaming his name and squirting on his face.
the next day they have received a noise complaint in their dorm and have to awkwardly lie about blasting porn in the middle of the night so robby can keep his dignity.
im gonna make dennis a self-committed slave to robby's old man pussy tonight, I can feel it. dennis is going to sob while eating him out and sucking on his t-dick and breathing in his musk because robby has a massive bush... robby will just smile down at his special boy and push his face deeper into his pussy... it's time.